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DE572267C - Process for the production of condensation products from formaldehyde and urea with the use of condensation products from phthalic anhydride and polyhydric alcohols - Google Patents

Process for the production of condensation products from formaldehyde and urea with the use of condensation products from phthalic anhydride and polyhydric alcohols

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Publication number
DE572267C
DE572267C DEG73881D DEG0073881D DE572267C DE 572267 C DE572267 C DE 572267C DE G73881 D DEG73881 D DE G73881D DE G0073881 D DEG0073881 D DE G0073881D DE 572267 C DE572267 C DE 572267C
Authority
DE
Germany
Prior art keywords
condensation products
urea
formaldehyde
phthalic anhydride
polyhydric alcohols
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DEG73881D
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German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DR RUDOLF MAYRHOFER
RUDOLF MAYRHOFER DR
Original Assignee
DR RUDOLF MAYRHOFER
RUDOLF MAYRHOFER DR
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DR RUDOLF MAYRHOFER, RUDOLF MAYRHOFER DR filed Critical DR RUDOLF MAYRHOFER
Priority to DEG73881D priority Critical patent/DE572267C/en
Priority to CH144877D priority patent/CH144877A/en
Priority to AT126144D priority patent/AT126144B/en
Application granted granted Critical
Publication of DE572267C publication Critical patent/DE572267C/en
Expired legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/46Block or graft polymers prepared by polycondensation of aldehydes or ketones on to macromolecular compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Description

Verfahren zur Herstellung von Kondensationsprodukten aus Formaldehyd und Harnstoff unter Mitverwendung von Kondensationsprodukten aus Phthalsäureanhydrid und mehrwertigen Alkoholen Die Erfindung betrifft ein Verfahren zur Herstellung von Kondensationsprodukten aus Formaldehyd und Harnstoff unter Mitverwendung von Kondensationsprodukten aus Phthalsäureanhydrid und mehrwertigen Alkoholen, insbesondere Glycerin, und bezweckt die Erzielung klar durchsichtiger, kunstglasähnlicher Massen. Dies wird gemäß der Erfindung dadurch erreicht, daß man den Harnstoff - Formaldehyd - Kondensationsprodukten, vorzugsweise während ihrer Bildung, hochviskose Kondensationsprodukte aus Phthalsäureanhydrid und mehrwertigen Alkoholen, insbesondere Glycerin, im Unterschuß zusetzt, derart, daß das Gewichtsverhältnis von Harnstoff zu Phthalsäureanhydrid .erheblich größer als i ist, wobei im alkalischen oder sauren Medium bzw. nacheinander alkalisch und dann sauer gearbeitet wird. Man erhält auf diese Weise gießbare Produkte, welche leicht zu vollkommen durchsichtigen Formlingen erstarren und diese Eigenschaft auch bei der etwaigen darauffoigenden Härtung bei erhöhter Temperatur beibehalten.Process for the production of condensation products from formaldehyde and urea with the use of condensation products from phthalic anhydride and polyhydric alcohols The invention relates to a method of preparation of condensation products from formaldehyde and urea with the use of Condensation products from phthalic anhydride and polyhydric alcohols, in particular Glycerin, and aims to achieve clear, transparent, art-glass-like masses. According to the invention, this is achieved by using the urea-formaldehyde - Condensation products, preferably highly viscous condensation products during their formation from phthalic anhydride and polyhydric alcohols, especially glycerine, in deficit adds, such that the weight ratio of urea to phthalic anhydride .Significantly greater than i, in an alkaline or acidic medium or in succession alkaline and then acidic. In this way, pourable products are obtained, which easily solidify to completely transparent bricks and this property retained even in the event of subsequent hardening at elevated temperature.

Es ist bereits vorgeschlagen worden, Kondensationsprodukte aus Phthalsäure und Glycerin unter Zusatz von Harnstoff und Formaldehyd oder dem Kondensationsprodukt aus diesen herzustellen. Hierbei wird Jedoch stets mit einem Überschuß an Phthalsäureanhydri.d, bezogen auf den Harnstoff, und ferner im neutralen Medium gearbeitet, so daß völlig andersartigeProdukte entstehen, welche balsamartige, d. h. viskose Massen darstellen, die nicht ohne weiteres zu festen, glasklar durchsichtigen Produkten erstarren. Dieser wesentliche Unterschied ist vermutlich darauf zurückzuführen, daß der freie oder noch im unvollständigen Stadium der Kondensation befindliche Harnstoff mit den noch freien Hydroxylgruppen der zugesetzten Phthalsäure-Glycerin-Kondensationsprodukte reagieren kann, so daß eine chemische Verkettung der Phthalsäure-Glycerin-Kondensationsprodukte mit den Harnstoff-Formaldehyd-Kondensationsproduktert und nicht etwa bloß die Bildung einer festen Lösung stattfindet. Ausführungsbeispiele i. Man erhitzt 22o Gewichtsteile Glycerin mit .go: Gewichtsteilen Phthalsäureanhydrid so lange, bis sich alles gelöst hat, unter Umschütteln und kocht dann noch etwa 5 bis 7 Stunden und gibt von diesem Produkt, zweckmäßig noch heiß, zu einem Kondensationsprodukt aus Formaldehyd und Harnstoff gemäß folgender Vorschrift: 8o g polymerer Formaldehyd, 59 g Harnstoff, 45 g Glycerin und 3o g Wasser werden gemischt und dann . nach Zugabe einiger Tropfen einer gesättigten Natriumcarbonatlösung längere Zeit zum Sieden erhitzt. Jetzt setzt man 30 g des wie oben beschrieben hergestellten Kondensationsproduktes zu, kocht wieder einige Zeit und gibt schließlich so viel Schwefelsäure zu, daß gerade schwach saure Reaktion eintritt. Man kocht noch kurze Zeit und gießt das nun klare, dünnflüssige Kondensationsprodukt in Formen. Die erstarrten Formlinge werden evtl. bei erhöhter-Temperatur gehärtet.It has already been proposed to produce condensation products from phthalic acid and glycerol with the addition of urea and formaldehyde or the condensation product from these. However, an excess of phthalic anhydride is always used, based on the urea, and also in a neutral medium, so that completely different products are created, which are balsamic, i.e. viscous masses that do not readily solidify into solid, crystal-clear, transparent products. This essential difference is probably due to the fact that the urea which is free or is still in the incomplete state of condensation can react with the still free hydroxyl groups of the added phthalic acid-glycerol condensation products, so that a chemical linkage of the phthalic acid-glycerol condensation products with the urea Formaldehyde condensation products and not just the formation of a solid solution. Embodiments i. 220 parts by weight of glycerol are heated with .go: parts by weight of phthalic anhydride until everything has dissolved, with shaking, and then boiled for about 5 to 7 hours and then added this product, expediently still hot, to a condensation product of formaldehyde and urea according to the following Prescription: 80 g of polymeric formaldehyde, 59 g of urea, 45 g of glycerin and 3o g of water are mixed and then. after adding a few drops of a saturated sodium carbonate solution heated to boiling for a long time. 30 g of the condensation product prepared as described above are now added, the mixture is boiled again for some time and finally enough sulfuric acid is added that a weakly acidic reaction occurs. The mixture is boiled for a short time and the condensation product, which is now clear, is poured into molds. The solidified briquettes may be hardened at an elevated temperature.

z. Das Kondensationsprodukt aus Glycerin und Phthalsäüreanhydrid wird wie in Beispiel i hergestellt. - 8o g polymerer Formaldehyd, 9o g Harnstoff, 8o g Wasser, 3 ccm einer a n-Sodalösung werden wie oben durch Erhitzen kondensiert. Dann werden 16o g des Phthalsäureanhydrid - Glycerin - Kondensationsproduktes zugegeben. Schließlich wird wie oben nach Zusatz von 5 ccm 2 n-Schwefelsäure die Kondensation zu Ende geführt.z. The condensation product of glycerol and phthalic anhydride is manufactured as in example i. - 8o g polymeric formaldehyde, 9o g urea, 8o g water, 3 ccm of an a n-soda solution are condensed as above by heating. Then 160 g of the phthalic anhydride-glycerol condensation product are added. Finally, as above, after the addition of 5 cc of 2 n-sulfuric acid, the condensation takes place brought to the end.

3. - 285 g polymerer Formaldehyd, 3 15 g Harnstoff, 335 g 4o°/oiger Formaldehyd werden gemischt und dann nach Zugabe von 1,5 g Natriumcarbonat oder der entsprechenden Menge Bariumhydroxyd längere Zeit zum Sieden erhitzt. Nach einiger Zeit setzt man i oo g de's wie . in Beispiel i beschriebenen Kondensationsproduktes aus ioo Gewichtsteilen Glycerin und iooGewichtsteilenPhthalsäureanhydrid zu. Dann kocht man noch etwa 2o Minuten und gießt dann in die Form.3. - 285 g of polymeric formaldehyde, 3 1 5 g of urea, 335 g 4o ° / cent formaldehyde are mixed and then heated to boiling for a longer time after the addition of 1.5 g sodium carbonate or the corresponding amount of barium hydroxide. After a while you put i oo g de's like. in Example i described condensation product of 100 parts by weight of glycerol and 100 parts by weight of phthalic anhydride. Then cook for about 20 minutes and then pour into the mold.

4. - 400 g polymerer Formaldehyd, 400 g Harnstoff, ioo g Wasser und ioo g Glycerin werden gemischt und nach Zugabe von io ccm 4 n-Schwefelsäure oder Salzsäure . längere Zeit zum Sieden erhitzt. Dann setzt man i 5o g eines Kondensationsproduktes aus 22o g Glycerin und 225 g Phthalsäüreanhydrid zu, kocht noch kurze Zeit und gießt dann in die Form.4. - 400 g of polymeric formaldehyde, 400 g of urea, 100 g of water and 100 g of glycerine are mixed and, after adding 10 ccm of 4 n-sulfuric acid or Hydrochloric acid. heated to boiling for a long time. Then i 50 g of a condensation product are used from 220 g of glycerol and 225 g of phthalic anhydride, cooks for a short time and pours then into the mold.

5. 335 g polymerer Formaldehyd, 165 g 40%iger Formaldehyd und 3009 Harnstoff werden gemischt und nach Zugabe von 2o ccm a n-Natriumcarbonatlösung oder der entsprechenden Menge Natriumhydroxyd längere Zeit zum Sieden erhitzt. Dann setzt man 45og eines Kondensationsproduktes aus 44o g Glykol und i8o g Phthalsäureanhydrid zu. Nach etwa albstündigem Kochen gibt man 2o ccm 2 n-Schwefelsäure oder Salzsäure zu, erhitzt noch kurze Zeit urid gießt dann in die Form.5. 335 g of polymeric formaldehyde, 165 g of 40% formaldehyde and 3009 urea are mixed and, after adding 2o ccm of n-sodium carbonate solution or the corresponding amount of sodium hydroxide, heated to the boil for a longer period of time. 45og of a condensation product of 44o g of glycol and 180 g of phthalic anhydride are then added. After boiling for about an hour, 2o ccm of 2N sulfuric acid or hydrochloric acid are added, heated for a short time and then poured into the mold.

Claims (1)

PPAATEN'TANSPRUCI3: Verfahren zur Herstellung von Kondensationsprodukten aus Formaldehyd und Harnstoff unter Mitverwendung von Konddnsationsprodukten aus Phthalsäureanhydrid und mehrwertigen. Alkoholen, insbesondere Glycerin, dadurch gekennzeichnet, daß man den Harnstoff-Formaldehyd-Kondensationsprodukten,vorzugsweise während ihrer Bildung, die hochviskosen Kondensationsprodukte aus Phthalsäureanhydrid und mehrwertigen Alkoholen, insbesondere Glycerin, im Unterschuß zusetzt, derart, daß das Gewichtsverhältnis von Harnstoff zu Phthalsäureanhydrid erheblich größer als i ist, wobei im alkalischen oder sauren bzw. nacheinander im alkalischen und dann im sauren Medium gearbeitet wird.PPAATEN'TANSPRUCI3: Process for the production of condensation products from formaldehyde and urea with the use of condensation products Phthalic anhydride and polyvalent. Alcohols, especially glycerine, thereby characterized in that the urea-formaldehyde condensation products, preferably during their formation, the highly viscous condensation products of phthalic anhydride and polyhydric alcohols, especially glycerine, added in deficit, such as that the weight ratio of urea to phthalic anhydride is considerably greater as i, where in alkaline or acidic or successively in alkaline and then work is carried out in the acidic medium.
DEG73881D 1928-07-23 1928-07-23 Process for the production of condensation products from formaldehyde and urea with the use of condensation products from phthalic anhydride and polyhydric alcohols Expired DE572267C (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DEG73881D DE572267C (en) 1928-07-23 1928-07-23 Process for the production of condensation products from formaldehyde and urea with the use of condensation products from phthalic anhydride and polyhydric alcohols
CH144877D CH144877A (en) 1928-07-23 1929-07-19 Process for the production of shaped condensation products.
AT126144D AT126144B (en) 1928-07-23 1929-07-20 Process for the production of art glass-like structures.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEG73881D DE572267C (en) 1928-07-23 1928-07-23 Process for the production of condensation products from formaldehyde and urea with the use of condensation products from phthalic anhydride and polyhydric alcohols

Publications (1)

Publication Number Publication Date
DE572267C true DE572267C (en) 1933-03-15

Family

ID=7135651

Family Applications (1)

Application Number Title Priority Date Filing Date
DEG73881D Expired DE572267C (en) 1928-07-23 1928-07-23 Process for the production of condensation products from formaldehyde and urea with the use of condensation products from phthalic anhydride and polyhydric alcohols

Country Status (3)

Country Link
AT (1) AT126144B (en)
CH (1) CH144877A (en)
DE (1) DE572267C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE751600C (en) * 1939-03-23 1953-05-11 Chemische Ind Ges Process for the production of alkyd-aminotriazinaldehyde mixed resins

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE751600C (en) * 1939-03-23 1953-05-11 Chemische Ind Ges Process for the production of alkyd-aminotriazinaldehyde mixed resins

Also Published As

Publication number Publication date
CH144877A (en) 1931-01-31
AT126144B (en) 1932-01-11

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